Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29289-13-2, name is 2-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., category: iodides-buliding-blocks
A) A mixture of K2CO3 (1.78 g, 12.9 mmol), CuI (61 mg, 5 mol %), 2-iodo-4-methylaniline (1.50 g, 6.44 mmol), N,N’-dimethylethylendiamine (0.14 mL, 20 mol%) and diethyl phosphite (1.04 mL, 8.11 mmol) in toluene (20 mL) was heated unter nitrogen atmosphere for 14h at 110 C. After cooling to room temperature, insolubles were separated by filtration and the residue washed with small portions of toluene. The major part of the solvent was removed in vacuum and the residue purified by column chromatography on silica gel using hexane / 5% ethyl acetate for elution yielding 1.02 g (65%) pale yellow oil. B) A mixture of Pd(PPh3)4 (149 mg, 2 mol %), 2-bromo-4-methyl-aniline (1.20 g, 6.45 mmol), Et3N (1.1 mL, 7.89 mmol) and diethyl phosphite (1.10 mL, 8.60 mmol) in toluene (20 mL) was heated under nitrogen atmosphere for 14h at 100 C and worked up as described in A) to give 1.19 g (76 %) pale yellow oil. 1H NMR (CDCl3): d 1.30 (t, 3J = 7.0 Hz, 6 H, CH3), 2.19 (s, 3 H, 5-CH3), 4.06 (m, 4 H, OCH2), 4.95 (br s, 2 H, NH2), 6.56 (dd, 3J = 8.1, 4JPH = 6.9 Hz, 1 H, H-3), 7.06 (dt, 3J = 8.3, 4J + 5JPH = 1.8 Hz, 1 H, H-4), 7.23 (dd, 3JPH = 14.7, 4J = 1.9 Hz, 1 H, H-6). 13C{1H} NMR (CDCl3): d 16.16 (d, 3J = 6.6 Hz, CH3), 20.09 (s, 5-CH3), 61.77 (d, 2J = 4.0 Hz, OCH2), 107.80 (d, 1J = 183.1 Hz, Cq-1), 116.35 (d, 3J = 13.3 Hz, C-3), 125.84 (d, 3J = 13.3 Hz, Cq-5), 132.80 (d, 2J = 6.6 Hz, C-6), 134.72 (d, 4J = 2.7 Hz, C-4), 148.79 (d, 2J = 8.0, Cq-2). 31P{1H} NMR (CDCl3): d 21.5. HRMS (ESI in MeOH+FA): C11H18NO3P (243.24), calcd. for [M+H]+ 244.1097; found: 244.1099.
According to the analysis of related databases, 29289-13-2, the application of this compound in the production field has become more and more popular.
Reference:
Article; Ghalib, Mohammed; Niaz, Basit; Heinicke, Joachim W.; Jones, Peter G.; Tetrahedron Letters; vol. 53; 37; (2012); p. 5012 – 5014,3;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com